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Biphenomycin B and Derivatives: Total Synthesis and Translation Inhibition

Authors

  • Dr. Yu-Peng He,

    1. Max-Planck-Institute of Molecular Physiology, Department of Chemical Biology, Otto-Hahn-Straße 11,D-44227 Dortmund (Germany), Fax: (+49) 231-133-2498
    2. Technische Universität Dortmund, Faculty of Chemistry, Otto-Hahn-Straße 6,D-44221 Dortmund (Germany)
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  • Hao Tan,

    1. Max-Planck-Institute of Molecular Physiology, Department of Chemical Biology, Otto-Hahn-Straße 11,D-44227 Dortmund (Germany), Fax: (+49) 231-133-2498
    2. Technische Universität Dortmund, Faculty of Chemistry, Otto-Hahn-Straße 6,D-44221 Dortmund (Germany)
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  • Dr. Lars Arve,

    1. Max-Planck-Institute of Molecular Physiology, Department of Chemical Biology, Otto-Hahn-Straße 11,D-44227 Dortmund (Germany), Fax: (+49) 231-133-2498
    2. Technische Universität Dortmund, Faculty of Chemistry, Otto-Hahn-Straße 6,D-44221 Dortmund (Germany)
    3. Current address: BayerCropScience GmbH, Alfred-Nobel-Straße 50, D-40789 Monheim (Germany)
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  • Dr. Sascha Baumann,

    1. Max-Planck-Institute of Molecular Physiology, Department of Chemical Biology, Otto-Hahn-Straße 11,D-44227 Dortmund (Germany), Fax: (+49) 231-133-2498
    2. Technische Universität Dortmund, Faculty of Chemistry, Otto-Hahn-Straße 6,D-44221 Dortmund (Germany)
    3. Current address: Stanford University School of Medicine, Department of Biochemistry, 279 Campus Drive, West Beckman Center, B469, Stanford, CA 94305-5307 (USA)
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  • Prof. Dr. Herbert Waldmann,

    Corresponding author
    1. Max-Planck-Institute of Molecular Physiology, Department of Chemical Biology, Otto-Hahn-Straße 11,D-44227 Dortmund (Germany), Fax: (+49) 231-133-2498
    2. Technische Universität Dortmund, Faculty of Chemistry, Otto-Hahn-Straße 6,D-44221 Dortmund (Germany)
    • Max-Planck-Institute of Molecular Physiology, Department of Chemical Biology, Otto-Hahn-Straße 11,D-44227 Dortmund (Germany), Fax: (+49) 231-133-2498

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  • Dr. Hans-Dieter Arndt

    Corresponding author
    1. Max-Planck-Institute of Molecular Physiology, Department of Chemical Biology, Otto-Hahn-Straße 11,D-44227 Dortmund (Germany), Fax: (+49) 231-133-2498
    2. Technische Universität Dortmund, Faculty of Chemistry, Otto-Hahn-Straße 6,D-44221 Dortmund (Germany)
    3. New address: Friedrich-Schiller-Universität Jena, Lehrstuhl für Organische Chemie I, Humboldstrasse 10, D-07743 Jena (Germany)
    • Max-Planck-Institute of Molecular Physiology, Department of Chemical Biology, Otto-Hahn-Straße 11,D-44227 Dortmund (Germany), Fax: (+49) 231-133-2498

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Abstract

A full account on the synthesis of the antibiotic natural product biphenomycin B and several derivatives is reported, which employs a Suzuki coupling reaction of a free carboxylic acid and macrolactam formation as key transformations. Liberal exchange of the central amino acid was demonstrated. This procedure gave derivatives to study the influence of the polar side chain of the central amino acids on translation inhibition.

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